Record Information
Version2.0
Creation Date2012-05-31 13:46:47 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01173
Identification
Name:5'-Methylthioadenosine
Description:5-Methylthioadenosine is a normal metabolite in Cysteine and methionine metabolism. Spermidine synthase (putrescine aminopropyltransferase)(EC:2.5.1.16) catalyzes the its formation and it is then converted to 5-Methylthio-D-ribose via S-adenosylhomocysteine/5'-methylthioadenosine nucleosidase [EC:3.2.2.9]. (KEGG)
Structure
Thumb
Synonyms:
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-b-D-ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-b-delta-ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-b-δ-ribofuranose
  • 1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-Ribofuranose
  • 1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-Ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-β-D-ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-β-δ-ribofuranose
  • 5'-(Methylthio)-5'-deoxyadenosine
  • 5'-(Methylthio)adenosine
  • 5'-S-methyl-5'-thioadenosine
  • 5'-Deoxy-5'-(methylthio)adenosine
  • 5'-Methylthioadenosine
  • 5'-S-Methyl-5'-thio-Adenosine
  • 5'-S-Methyl-5'-thioadenosine
  • 5-Methylthioadenosine
  • S-methyl-adenosine
  • Methylthioadenosine
  • MTA
  • S-Methyl-5'-thioadenosine
  • S-Methyl-5-thioadenosine
  • S-Methyl-adenosine
  • Thiomethyladenosine
Chemical Formula:C11H15N5O3S
Weight:Average: 297.334
Monoisotopic: 297.089560061
InChI Key:WUUGFSXJNOTRMR-IOSLPCCCSA-N
InChI:InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
CAS number:2457-80-9
IUPAC Name:(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
Traditional IUPAC Name:methylthioadenosine
SMILES:CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub Class5'-deoxyribonucleosides
Direct Parent5'-deoxy-5'-thionucleosides
Alternative Parents
Substituents
  • 5'-deoxy-5'-thionucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Primary aromatic amine
  • Pyrimidine
  • N-substituted imidazole
  • Monosaccharide
  • Imidolactam
  • Azole
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.5 mg/mLALOGPS
logP-0.14ALOGPS
logP-0.61ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.31 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.03 m3·mol-1ChemAxon
Polarizability29.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Glutathione metabolismPW000833 Pw000833Pw000833 greyscalePw000833 simple
Spermidine Biosynthesis IPW002040 Pw002040Pw002040 greyscalePw002040 simple
aminopropylcadaverine biosynthesisPW002039 Pw002039Pw002039 greyscalePw002039 simple
beta-Alanine metabolismPW000896 Pw000896Pw000896 greyscalePw000896 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-000i-0940000000-16b1106966ac98c7a107View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-056r-9530000000-5fbf6b1a856ad3827980View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000i-0940000000-16b1106966ac98c7a107View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000i-0940000000-30fc68e7b5ff7576069bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-01ti-0900000000-312bd8eec3c461e919f9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0h70-9636300000-67e425eba97fe420c464View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000j-0940000000-55655e7a0a6c8acba0f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-f37865ca2029a623ace7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2900000000-ae0e3df9bf25c100940dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0090000000-72139812c5b2ede077edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-0910000000-0c3d173f36272e3271ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-0900000000-f3443ca133811f52c5d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-1900000000-49cc299525d7fca27818View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000i-3900000000-39bebdcaa7ce2695465bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-76b935f4f0a78c15ca0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0002-4900000000-d8c0df43305b934d71dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0900000000-d3bfbeb6fb95e3768ef6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0910000000-56784be58ef9065f21f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0910000000-56784be58ef9065f21f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0090000000-72139812c5b2ede077edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0910000000-0c3d173f36272e3271ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-f3443ca133811f52c5d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-6ec86a11bf8ad7331bd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-3900000000-39bebdcaa7ce2695465bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-b9006ef8eecdaefc89a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0940000000-eb168427f389d7079abfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-714e20a3376683008e65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-cb0adab85341c49ced5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9220000000-14da12fd68bc6d33eed9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910000000-324b5daf65bdaa0d2bdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-4900000000-14e9c89fcdd488f204aaView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Avila MA, Garcia-Trevijano ER, Lu SC, Corrales FJ, Mato JM: Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30. Pubmed: 15313459
  • Contreres JO, Dupuy E, Job B, Habib A, Bryckaert M, Rosa JP, Simoneau G, Herbert JM, Savi P, Levy-Toledano S: Effect of clopidogrel administration to healthy volunteers on platelet phosphorylation events triggered by ADP. Br J Haematol. 2003 Feb;120(4):633-42. Pubmed: 12588350
  • Gerasimovskaya EV, Ahmad S, White CW, Jones PL, Carpenter TC, Stenmark KR: Extracellular ATP is an autocrine/paracrine regulator of hypoxia-induced adventitial fibroblast growth. Signaling through extracellular signal-regulated kinase-1/2 and the Egr-1 transcription factor. J Biol Chem. 2002 Nov 22;277(47):44638-50. Epub 2002 Sep 18. Pubmed: 12244041
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. Pubmed: 9129323
  • Mills GC, Mills JS: Urinary excretion of methylthioadenosine in immunodeficient children. Clin Chim Acta. 1985 Mar 30;147(1):15-23. Pubmed: 3987052
  • Mills GC, Schmalstieg FC, Goldblum RM: Urinary excretion of modified purines and nucleosides in immunodeficient children. Biochem Med. 1985 Aug;34(1):37-51. Pubmed: 4052062
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Sufrin, Janice R.; Spiess, Arthur J.; Kramer, Debora L.; Libby, Paul R.; Porter, Carl W. Synthesis and antiproliferative effects of novel 5'-fluorinated analogs of 5'-deoxy-5'-(methylthio)adenosine. Journal of Medicinal Chemistry (1989), 32(5), 997-1001.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17509
HMDB IDHMDB01173
Pubchem Compound ID149
Kegg IDC00170
ChemSpider ID388321
Wikipedia IDNot Available
BioCyc ID5-METHYLTHIOADENOSINE
EcoCyc ID5-METHYLTHIOADENOSINE
Ligand ExpoMTA

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM), which serves as an aminopropyl donor
Gene Name:
speE
Uniprot ID:
P09158
Molecular weight:
32321
Reactions
S-adenosylmethioninamine + putrescine = 5'-S-methyl-5'-thioadenosine + spermidine.
General function:
Involved in adenosylhomocysteine nucleosidase activity
Specific function:
Catalyzes the irreversible cleavage of the glycosidic bond in both 5'-methylthioadenosine (MTA) and S- adenosylhomocysteine (SAH/AdoHcy) to adenine and the corresponding thioribose, 5'-methylthioribose and S-ribosylhomocysteine, respectively. Can also use 5'-isobutylthioadenosine, 5'-n- butylthioadenosine, S-adenosyl-D-homocysteine, decarboxylated adenosylhomocysteine, deaminated adenosylhomocysteine and S-2-aza- adenosylhomocysteine as substrates
Gene Name:
mtnN
Uniprot ID:
P0AF12
Molecular weight:
24354
Reactions
S-adenosyl-L-homocysteine + H(2)O = S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine.
S-methyl-5'-thioadenosine + H(2)O = S-methyl-5-thio-D-ribose + adenine.